Benzoyl chloride → HCID 131724329, compound

HRID 2119780Notes

Reaction equation

HRID 2119780 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([CH:14]([OH:44])[C@H:15]1[O:19][C@@H:18]([N:20]2[C:29]3[C:23]([C:24]([N:26]=[CH:27][N:28]=3)=[NH:25])=[N:22][C:21]2=[SiH2:30])[C@H:17]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C@@H:16]1[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:13])([CH3:12])[CH3:11].N1CCOCC1>N1C=CC=CC=1>[C:10]([CH:14]([OH:44])[C@H:15]1[O:19][C@@H:18]([N:20]2[C:29]3[C:23]([C:24]([N:26]=[CH:27][N:28]=3)=[N:25][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:22][C:21]2=[SiH2:30])[C@H:17]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C@@H:16]1[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8083MorpholineHCID 131724330HCID 131724330, compound

Product 1

HCID 131724329HCID 131724329, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzoyl chloride (8 ml, 68.86 mmol) was added dropwise to a stirred suspension of (50) (17.89 g, 34.28 mmol) in anhydrous pyridine (100 ml) at 0° C. After 5 min the reaction was warmed to room temperature and stirred for 2.5 hr. After that the mixture was cooled to 0° C. and morpholine (12 ml, 137.9 mmol) was added slowly with stirring. After 45 min at 0° C. the reaction mixture was evaporated and the residue was partitioned between methylene chloride and water. The organic layer was dried over sodium sulfate and evaporated in vacuo. Crystallization from acetonitrile (100 ml) furnished (51) as crystalline material. Yield 16.47 g (76.8%).

Workup

  1. temperatureAfter that the mixture was cooled to 0° C.
  2. stirringwith stirring
  3. customAfter 45 min at 0° C. the reaction mixture was evaporated
  4. customthe residue was partitioned between methylene chloride and water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customCrystallization from acetonitrile (100 ml)

Sources & evidence

ORD record
ord-ece6730cfba341c19ab6298e83fd9b67
Source dataset
uspto-grants-2004_02
Patent number
US06686463B2

Reaction notes

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